Cheshire Election 2025: Samantha Rosenberg Running For Board Of Education

CHESHIRE, CT — The 2025 municipal election is heating up in Cheshire with plenty of races on the ballot.

Voters will cast their ballots in the Nov. 4 election for seats on the Town Council, Board of Education, Planning and Zoning Commission and more.

Cheshire Patch asked candidates to answer questions about their campaigns and will be publishing candidate profiles as election day draws near.

Samantha Rosenberg is running for re-election to the Cheshire Board of Education as a Democrat.

Campaign Website
https://www.cheshiredem.org/

Occupation:

Education Administrator 17 years

Family:
Samantha Rosenberg has been a proud Cheshire resident for nearly 25 years. She and her husband, Adam, chose Cheshire for its outstanding educational opportunities and strong community values. All three of their children are alumni of Cheshire Public Schools: their oldest graduated from the University of Albany, their second from Bard College, and their youngest is currently attending Penn State University. The family is also joined by their 11-year-old dog, Mimi.

Does anyone in your family work in politics or government?
No

Previous public office, appointive or elective:
Board of Education

Why are you seeking this office?
Serving Cheshire has been an incredible honor, and I’m running for re-election because there’s still more work to do. Over the past four years as Chair of the Cheshire Board of Education, I’ve seen firsthand how local decisions shape the daily lives of our students, teachers, and families. What motivates me is ensuring Cheshire continues to be a community known for excellent schools, dedicated educators, and opportunities that prepare every student for success.

Together—with talented educators, engaged families, and dedicated town leaders—we’ve made historic progress and positioned Cheshire as one of Connecticut’s top-performing districts.

The single most pressing issue facing my constituents is ____, and this is what I intend to do about it:
The single most pressing issue facing my constituents is maintaining the high quality of education our community expects while managing increasing costs and evolving student needs. As our town grows and educational demands change, we must continue balancing fiscal responsibility with meaningful investment in our students, teachers, and facilities.

I intend to address this by continuing to lead with transparency, collaboration, and long-term planning—ensuring that every budget decision reflects community values and student success. That means advocating for smart investments in curriculum, mental health supports, and modernized learning environments, while keeping our schools strong, equitable, and future-ready.

What are the major differences between you and the other candidates seeking this post?
The major difference between me and the other candidates is my proven experience and results leading the Board through a period of historic progress and collaboration. As Chair, I’ve worked to strengthen academic achievement, support our educators, modernize our facilities, and ensure fiscal responsibility—all while keeping students at the center of every decision.

I believe effective leadership means listening, problem-solving, and building consensus. My focus has always been on what unites us: ensuring Cheshire remains a community known for excellent schools, strong values, and opportunities for every child to thrive.

What other issues do you intend to address during your campaign?
In addition to maintaining Cheshire’s high academic standards, I plan to focus on student wellness, educator support, and long-term strategic planning. That includes expanding mental health resources, investing in curriculum and career pathways, and ensuring our schools remain safe and modern. With two new elementary schools opening in time for the upcoming school year, my priority is to build on that momentum—modernizing the rest of our schools and facilities so every student learns in an environment that reflects Cheshire’s commitment to excellence. I’ll also continue to promote fiscal responsibility and open communication, ensuring families, educators, and residents have a strong voice in shaping the future of our district.

What accomplishments in your past would you cite as evidence you can handle this job?
My experience as Chair of the Cheshire Board of Education demonstrates my ability to lead collaboratively and effectively. During my tenure, our district has achieved record academic performance, strengthened student supports, and advanced major capital projects—including the construction of two new elementary schools.

Professionally, I serve as Director of Career & Community Learning for Stratford Public Schools, overseeing CTE and Adult/Continuing Education. I manage curriculum development, professional learning, grants, and partnerships that expand student opportunities and equitable access. With over 16 years as an educator and administrator—and 13 years prior in financial services—I bring both educational expertise and fiscal accountability to the role.

My leadership reflects Cheshire’s commitment to “Excellence in Education,” promoting lifelong learning, critical thinking, and community engagement.

What is the best advice anyone ever gave you?
“Listen first, speak second.”

In schools and boards, understanding perspectives before reacting helps build trust and make better decisions.

Is there anything else you would like voters to know about yourself and your positions?
I want voters to know that my commitment is to every student and every family in our community. I believe in thoughtful, collaborative decision-making, and I prioritize transparency, equity, and long-term planning. With two new schools opening soon and ongoing modernization needs, I am focused on ensuring all our students have safe, modern, and well-equipped learning environments. At the same time, I remain mindful of the ever-changing needs of our town and the importance of fiscal responsibility, making sure our resources are used wisely while listening to teachers, parents, and students so our schools can continue to grow and thrive for years to come.